KR20240052073A

KR20240052073A - 유기 전계 발광 소자

유기 전계 발광 소자 Download PDF

Info

Publication number: KR20240052073A
Authority: KR; South Korea
Prior art keywords: ring; aryl; carbon atoms; alkyl; heteroaryl
Prior art date: 2017-08-17

Application number

KR1020247011561A

Other languages

English (en)

Korean (ko)

Inventor

다쿠지 하타케야마

가쓰야 마스다

모토키 야나이

Original Assignee

가꼬우 호징 관세이 가쿠잉

에스케이머티리얼즈제이엔씨 주식회사

Priority date

2017-08-17

Filing date

2018-06-12

Publication date

2024-04-22

2018-06-12 Application filed by 가꼬우 호징 관세이 가쿠잉, 에스케이머티리얼즈제이엔씨 주식회사 filed Critical 가꼬우 호징 관세이 가쿠잉

2018-06-12 Priority claimed from KR1020197038426A external-priority patent/KR102701483B1/ko

2024-04-22 Publication of KR20240052073A publication Critical patent/KR20240052073A/ko

Links

-1 polycyclic aromatic compounds Chemical class 0.000 claims abstract description 604
125000003118 aryl group Chemical group 0.000 claims abstract description 489
125000000217 alkyl group Chemical group 0.000 claims abstract description 452
150000001875 compounds Chemical class 0.000 claims abstract description 411
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 362
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 206
239000001257 hydrogen Substances 0.000 claims abstract description 206
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 133
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 76
239000002019 doping agent Substances 0.000 claims abstract description 58
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 28
229910052805 deuterium Inorganic materials 0.000 claims abstract description 28
125000005647 linker group Chemical group 0.000 claims abstract description 25
229920000642 polymer Polymers 0.000 claims abstract description 22
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 20
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 525
125000003545 alkoxy group Chemical group 0.000 claims description 146
229910052736 halogen Chemical group 0.000 claims description 105
150000002367 halogens Chemical group 0.000 claims description 105
125000004093 cyano group Chemical group *C#N 0.000 claims description 95
125000004986 diarylamino group Chemical group 0.000 claims description 72
125000004104 aryloxy group Chemical group 0.000 claims description 70
238000002347 injection Methods 0.000 claims description 69
239000007924 injection Substances 0.000 claims description 69
125000005240 diheteroarylamino group Chemical group 0.000 claims description 52
229910052751 metal Inorganic materials 0.000 claims description 28
239000002184 metal Substances 0.000 claims description 28
125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 27
125000004665 trialkylsilyl group Chemical group 0.000 claims description 24
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 20
239000000539 dimer Substances 0.000 claims description 17
229910052783 alkali metal Inorganic materials 0.000 claims description 16
150000001340 alkali metals Chemical group 0.000 claims description 16
150000001454 anthracenes Chemical class 0.000 claims description 14
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
150000001342 alkaline earth metals Chemical class 0.000 claims description 13
HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 12
125000005103 alkyl silyl group Chemical group 0.000 claims description 12
150000001716 carbazoles Chemical class 0.000 claims description 12
150000004820 halides Chemical class 0.000 claims description 12
229910052761 rare earth metal Inorganic materials 0.000 claims description 11
150000002910 rare earth metals Chemical class 0.000 claims description 11
239000013638 trimer Substances 0.000 claims description 10
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 8
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 7
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
150000003222 pyridines Chemical class 0.000 claims description 7
150000003918 triazines Chemical class 0.000 claims description 7
150000003230 pyrimidines Chemical class 0.000 claims description 6
150000002219 fluoranthenes Chemical class 0.000 claims description 5
150000005041 phenanthrolines Chemical class 0.000 claims description 5
229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 4
XPJUXTZYXPASRB-UHFFFAOYSA-N benzo[f]pentahelicene Chemical class C1=CC=C2C3=C4C5=CC=CC=C5C=CC4=CC=C3C3=CC=CC=C3C2=C1 XPJUXTZYXPASRB-UHFFFAOYSA-N 0.000 claims description 4
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 14
239000010410 layer Substances 0.000 description 282
125000001424 substituent group Chemical group 0.000 description 152
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 120
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 104
239000000463 material Substances 0.000 description 96
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 95
239000010408 film Substances 0.000 description 92
238000005401 electroluminescence Methods 0.000 description 88
239000000758 substrate Substances 0.000 description 66
230000032258 transport Effects 0.000 description 64
238000006243 chemical reaction Methods 0.000 description 59
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 54
238000000151 deposition Methods 0.000 description 53
125000000753 cycloalkyl group Chemical group 0.000 description 52
230000008021 deposition Effects 0.000 description 49
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
229910052799 carbon Inorganic materials 0.000 description 38
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 37
238000000034 method Methods 0.000 description 34
229910052796 boron Inorganic materials 0.000 description 32
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
230000000052 comparative effect Effects 0.000 description 30
238000004519 manufacturing process Methods 0.000 description 30
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 29
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 29
125000001624 naphthyl group Chemical group 0.000 description 28
239000003480 eluent Substances 0.000 description 26
239000002994 raw material Substances 0.000 description 26
239000000243 solution Substances 0.000 description 26
229910052782 aluminium Inorganic materials 0.000 description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
239000000203 mixture Substances 0.000 description 25
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 24
230000005525 hole transport Effects 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
238000003786 synthesis reaction Methods 0.000 description 21
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000012299 nitrogen atmosphere Substances 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 18
239000011521 glass Substances 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 17
DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910052801 chlorine Inorganic materials 0.000 description 16
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
238000009833 condensation Methods 0.000 description 15
230000005494 condensation Effects 0.000 description 15
125000001041 indolyl group Chemical group 0.000 description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 15
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 15
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 14
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 14
125000000623 heterocyclic group Chemical group 0.000 description 14
239000000126 substance Substances 0.000 description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
229910052731 fluorine Inorganic materials 0.000 description 13
239000011737 fluorine Substances 0.000 description 13
229910052744 lithium Inorganic materials 0.000 description 13
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 13
125000000168 pyrrolyl group Chemical group 0.000 description 13
150000003459 sulfonic acid esters Chemical class 0.000 description 13
238000010189 synthetic method Methods 0.000 description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 12
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
229910052717 sulfur Inorganic materials 0.000 description 12
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 11
NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
125000003342 alkenyl group Chemical group 0.000 description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
125000002619 bicyclic group Chemical group 0.000 description 11
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 11
229910052760 oxygen Inorganic materials 0.000 description 11
239000001301 oxygen Substances 0.000 description 11
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 11
125000005561 phenanthryl group Chemical group 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000007740 vapor deposition Methods 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 10
125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 10
125000004429 atom Chemical group 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
125000005842 heteroatom Chemical group 0.000 description 10
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
125000002971 oxazolyl group Chemical group 0.000 description 10
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 10
238000004544 sputter deposition Methods 0.000 description 10
239000011593 sulfur Chemical group 0.000 description 10
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 10
125000005580 triphenylene group Chemical group 0.000 description 10
239000002841 Lewis acid Substances 0.000 description 9
125000003277 amino group Chemical group 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
125000003838 furazanyl group Chemical group 0.000 description 9
125000002883 imidazolyl group Chemical group 0.000 description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 9
125000000842 isoxazolyl group Chemical group 0.000 description 9
150000007517 lewis acids Chemical class 0.000 description 9
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 9
230000008569 process Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
125000003373 pyrazinyl group Chemical group 0.000 description 9
125000003226 pyrazolyl group Chemical group 0.000 description 9
125000000714 pyrimidinyl group Chemical group 0.000 description 9
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 9
238000006467 substitution reaction Methods 0.000 description 9
125000003831 tetrazolyl group Chemical group 0.000 description 9
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 8
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 8
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 8
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 8
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
125000005577 anthracene group Chemical group 0.000 description 8
235000010290 biphenyl Nutrition 0.000 description 8
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 8
239000000470 constituent Substances 0.000 description 8
PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 8
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 8
238000011156 evaluation Methods 0.000 description 8
230000006872 improvement Effects 0.000 description 8
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 8
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 8
239000011159 matrix material Substances 0.000 description 8
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 8
238000005498 polishing Methods 0.000 description 8
125000004076 pyridyl group Chemical group 0.000 description 8
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 7
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
125000004391 aryl sulfonyl group Chemical group 0.000 description 7
125000000732 arylene group Chemical group 0.000 description 7
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 description 7
150000002739 metals Chemical class 0.000 description 7
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
125000001715 oxadiazolyl group Chemical group 0.000 description 7
230000001603 reducing effect Effects 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910052715 tantalum Inorganic materials 0.000 description 7
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 7
239000010409 thin film Substances 0.000 description 7
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
239000004305 biphenyl Substances 0.000 description 6
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
229910052792 caesium Inorganic materials 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
125000002541 furyl group Chemical group 0.000 description 6
125000004430 oxygen atom Chemical group O* 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
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